Acetonitrile → HCID 15233540, compound

HRID 1653658Notes

Reaction equation

HRID 1653658 reaction equation
[CH3:1][C:2]1([CH3:17])[C:10]2[C:5](=[C:6](C)[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=2)[C:4]([CH3:15])([CH3:14])[CH:3]1[CH3:16].S(OOS([O-])(=O)=O)([O-])(=O)=[O:19].[K+].[K+].C(Cl)Cl.[C:33](#N)[CH3:34]>O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH:6]([C:7]1[C:33]([CH3:34])=[C:5]2[C:10](=[CH:9][C:8]=1[O:11][CH3:12])[C:2]([CH3:17])([CH3:1])[CH:3]([CH3:16])[C:4]2([CH3:15])[CH3:14])=[O:19]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 24412Potassium PersulfateHCID 15233539HCID 15233539, compound

Product 1

HCID 15233540HCID 15233540, compound

Reagents, catalysts & solvents 2

HCID 24463Copper sulfate pentahydrateCatalystHCID 962WaterSolvent

Procedure

The 1,1,2,3,3,4-hexamethyl-6-methoxyindane (10.8 g) is then heated with copper(II) sulfate pentahydrate (18.04 g) and potassium peroxydisulfate (60.55 g) in acetonitrile and water (1:1, 500 ml) at reflux for about 15 to 20 minutes, following procedures similar to those described in Hauser et al., Synthesis, pp. 723-724 (1987). The mixture is then cooled to room temperature and methylene chloride (150 ml) is added. The layers are separated and the aqueous phase is further extracted with additional methylene chloride (2×70 ml). The combined organic solutions are dried with anhydrous sodium sulfate, filtered, and evaporated at reduced pressure to yield 5-formyl-1,1,2,3,3,4-hexamethyl-6-methoxyindane.

Workup

  1. temperatureat reflux for about 15 to 20 minutes
  2. customthose described in Hauser et al., Synthesis
  3. customThe layers are separated
  4. extractionthe aqueous phase is further extracted with additional methylene chloride (2×70 ml)
  5. dry with materialThe combined organic solutions are dried with anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated at reduced pressure

Sources & evidence

ORD record
ord-be748358ad8f4af399b1102cd3bc6b65
Source dataset
uspto-grants-1995_04
Patent number
US05403823

Reaction notes

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